S-(2-Acetamidoethyl) hexadecanethioate

Identification

Name
S-(2-Acetamidoethyl) hexadecanethioate
Accession Number
DB02990  (EXPT03058)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • C16-fatty-acyl-substrate-mimic
  • S-palmitoyl-N-acetylcysteamine
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 357.594
Monoisotopic: 357.270150187
Chemical Formula
C20H39NO2S
InChI Key
GDVZALUOXPTSHD-UHFFFAOYSA-N
InChI
InChI=1S/C20H39NO2S/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(23)24-18-17-21-19(2)22/h3-18H2,1-2H3,(H,21,22)
IUPAC Name
N-[2-(hexadecanoylsulfanyl)ethyl]acetamide
SMILES
CCCCCCCCCCCCCCCC(=O)SCCNC(C)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEnoyl-[acyl-carrier-protein] reductase [NADH]Not AvailableMycobacterium tuberculosis
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
3378216
PubChem Substance
46508640
ChemSpider
2623508
ZINC
ZINC000014880555
PDBe Ligand
THT
PDB Entries
1bvr

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000217 mg/mLALOGPS
logP7.27ALOGPS
logP5.92ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)15.78ChemAxon
pKa (Strongest Basic)-0.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.17 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity105.75 m3·mol-1ChemAxon
Polarizability46.41 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9972
Blood Brain Barrier+0.9957
Caco-2 permeable+0.6172
P-glycoprotein substrateNon-substrate0.6473
P-glycoprotein inhibitor INon-inhibitor0.6522
P-glycoprotein inhibitor IINon-inhibitor0.9291
Renal organic cation transporterNon-inhibitor0.8614
CYP450 2C9 substrateNon-substrate0.8245
CYP450 2D6 substrateNon-substrate0.7164
CYP450 3A4 substrateNon-substrate0.6387
CYP450 1A2 substrateNon-inhibitor0.5177
CYP450 2C9 inhibitorNon-inhibitor0.7847
CYP450 2D6 inhibitorNon-inhibitor0.9046
CYP450 2C19 inhibitorNon-inhibitor0.7544
CYP450 3A4 inhibitorNon-inhibitor0.9288
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8667
Ames testNon AMES toxic0.8712
CarcinogenicityNon-carcinogens0.6326
BiodegradationReady biodegradable0.7363
Rat acute toxicity2.1627 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9595
hERG inhibition (predictor II)Non-inhibitor0.7908
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as fatty acyl thioesters. These are thioester derivatives of a fatty acid with the general formula RC(=O)SR', where R is the fatty acyl chain.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acyl thioesters
Direct Parent
Fatty acyl thioesters
Alternative Parents
Acetamides / Thioesters / Secondary carboxylic acid amides / Carbothioic S-esters / Sulfenyl compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Acetamide / Aliphatic acyclic compound / Carbonyl group / Carbothioic s-ester / Carboxamide group / Carboxylic acid derivative / Fatty acyl thioester / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Enoyl-ACP reductase of the type II fatty acid syntase (FAS-II) system, which is involved in the biosynthesis of mycolic acids, a major component of mycobacterial cell walls (PubMed:25227413). Catalyzes the NADH-dependent reduction of the double bond of 2-trans-enoyl-[acyl-carrier protein], an essential step in the fatty acid elongation cycle of the FAS-II pathway (PubMed:7599116). Shows preference for long-chain fatty acyl thioester substrates (>C16), and can also use 2-trans-enoyl-CoAs as alternative substrates (PubMed:7599116). The mycobacterial FAS-II system utilizes the products of the FAS-I system as primers to extend fatty acyl chain lengths up to C56, forming the meromycolate chain that serves as the precursor for final mycolic acids (PubMed:25227413).
Specific Function
Enoyl-[acyl-carrier-protein] reductase (nadh) activity
Gene Name
inhA
Uniprot ID
P9WGR1
Uniprot Name
Enoyl-[acyl-carrier-protein] reductase [NADH]
Molecular Weight
28527.55 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:52

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